Sig Mosley typically drinks red wine, but on this day in December 1999, he was also drinking Champagne.
A few years before, Mosley had cut a $500,000 check to take a stake in a startup e-commerce company. But a few days before Christmas 25 years ago, he found himself toasting its sale in a deal that would eventually be worth $5.7 billion.
Mosley, then 53, with a boyish face, was rich.
But what do you do after making the biggest deal of your life?
Some might buy a yacht and retire. Mosley took another path. A son of North Georgia with an up-by-his-bootstraps bio became an investor in other bootstrapping companies, a decision still shaping metro Atlanta’s technology scene today.
Meeting his mentor
Mosley is a Georgia boy through and through. He grew up in Jasper, a small city 50 miles north of Atlanta nestled in the mountains. He was an only child, the son of a salesman and a stay-at-home-mom, but his family extended through the town.
“I were kin to 85% of them some way,” Mosley, now 78, told The Atlanta Journal-Constitution.
In the 1960s, he made his way from Jasper to Emory University. He had known he wanted to be in business someway, but once he took one accounting course, he was hooked.
After graduating, he had a short stint as an auditor before joining Atlanta-based Management Science America as an accountant in 1969. He spent the next 21 years of his career at the computer software company. It’s where he met John Imlay, the head of MSA who had brought the company out of bankruptcy and who would usher Mosley into the world of venture investing.
Imlay and Mosley were opposites in many ways. Mosley was quieter, a numbers guy more at home in the background. Imlay, who died in 2015, was brash and gregarious with a flair for the dramatic. He once rode a horse across the stage of the Fox Theatre for a speech to motivate his employees. He also used more daring props, like chimpanzees, elephants and big cats, in his talks.
Mosley recalled one annual meeting at the East Lake Golf Course in the early 1970s where Imlay decided to use an actual tiger during his speech. A server carrying a tray of glasses came up the stairs of the club, turned the corner and was surprised by the cat.
“I am told on good sources that he were down and out the back door before the glasses hit the ground,” Mosley said with a chuckle.
Credit: Handout
Credit: Handout
But he and Imlay made a good team. Mosley rose through the ranks to eventually become a vice president, secretary and treasurer of MSA. In 1989, 10 years before Imlay and Mosley struck their big deal, MSA was acquired by Dun & Bradstreet for more than $300 million. Imlay got $53 million from the deal and decided to forge a new path, bringing Mosley along.
The $5.7 billion deal
With his post-MSA windfall, Imlay wanted to set up a personal office to handle his funds and give back to the entrepreneurial community, so Mosley put together a plan and became the head of Imlay Investments. The focus was on angel investing, cutting checks to early stage startups, typically the first investment they got and often long before they were profitable. Imlay wanted to support technology companies in the Southeast, primarily Atlanta.
Then, as now, Atlanta’s venture capital ecosystem wasn’t large. But Imlay and Mosley built a reputation for nurturing companies whether they invested in them or not.
Throughout the 1990s, Mosley invested in dozens of companies, on average $100,000 to $200,000 at a time. One of the companies, Internet Security Systems, even went public, netting Imlay Investments 30 times what it put in.
But one investment would make Mosley a legend.
In 1996, he put $500,000 — one of the biggest investments he’d made to date — into a small startup based in Tampa, Fla., at the time, Tradex. He liked the founder, Daniel Aergerter, but didn’t like his business model.
So, Aergerter changed his strategy, turning Tradex into an e-commerce platform for businesses. He also moved to Atlanta, and Mosley joined the company’s board. Three years after he invested in the startup, online procurement company Ariba came knocking to acquire Tradex.
The deal itself was a gamble. It didn’t lay out a specific dollar amount Tradex and its investors would receive in the acquisition, but rather it set a number of shares they’d get in the combined company. If the company’s stock tanked, then Mosley and the Tradex team would eat the loss. But if the stock rose, they got the gain.
And rose it did. Between December 1999, when the deal was signed, to March 2000, when it closed, Ariba’s stock approximately tripled at the height of the dot-com bubble. That meant that within three months, the acquisition went from being worth $1.8 billion to $5.7 billion, which is more than $10 billion in today’s dollars. To this day it is still considered the largest tech venture deal in the Southeast.
For Mosley, Tradex’s trajectory was a surprise. He never thought it would turn into a multibillion-dollar company.
“If anybody had told me that, I would have told them they were crazy,” he said. But he trusted his gut and his belief in the founder.
Mosley has never disclosed how much money Imlay Investments made from the acquisition, but he said that for every dollar they put in, they got $180 back.
Many would sail into the sunset after getting the return from a multibillion-dollar acquisition. But not Mosley. The goal after the acquisition was to continue investing in startups.
Then the dot-com bubble burst.
The godfather
The precipitous decline in the fortunes of technology startups meant that after the biggest deal of his career, Mosley was suddenly barely investing. He said he only cut one check in 2001 when he had been averaging about 12 deals a year up to that point.
But the end of the dot-com era and the pullback from investors made Mosley want to continue his work even more.
“Part of what we were doing was investing to help build the economy and the tech community here,” he said. “Right after the (Tradex) deal we had the dot-com bust, and so it was a challenging time. … We needed to be in the community, and we needed to be investing.”
Since the Tradex acquisition, Mosley has become known as the “godfather of angel investing” in Atlanta. Over the course of his career, he’s invested in 120 startups, including software companies Knowlagent and Synchrologic, and has had 82 exits, a high success rate.
When asked about Mosley, entrepreneurs and investors in Atlanta say three things: he is humble, always willing to listen and generous with his time.
That doesn’t mean he says yes to every deal, but it’s a badge of honor to even get a no from him. It’s not uncommon to see Atlanta founders wearing a T-shirt emblazoned with “Sig said no,” signaling that Mosley had deigned to listen to their pitch.
Mosley said he’d look at 100 companies just to make one investment. But whether he wrote a check or not, he would always try to help any of the entrepreneurs with whom he talked.
“I never cut somebody down,” he said. “Even if I think they’re horrible, I won’t tell them that.”
Credit: Atlanta Journal-Constitution
Credit: Atlanta Journal-Constitution
In 2005, David Cummings, the serial entrepreneur who founded the Atlanta Tech Village, Atlanta Ventures and now owns a large swath of South Downtown, was a young startup founder who had hit $1 million in revenue with his first company. Now, he thought, was the time to seek out angel investment. He was told to talk to Mosley.
“I was a little in awe going into the big, fancy office as the scrappy, bootstrapped entrepreneur, just, you know, trying to keep the lights on, but feeling pretty good about the progress that had been made,” Cummings recalled.
Mosley was kind and listened to the pitch but ultimately said no.
“For me, as somebody who’s very much a product and sales and marketing person, I wasn’t as brushed up as I should have been on the finance and accounting side of the business. And so that was a good lesson learned for me,” Cummings said.
But that first meeting was just the beginning of Mosley and Cummings’ relationship. In 2012, Mosley started his own venture firm, Mosley Ventures, a few years before stepping down as president of Imlay Investments.
In 2013, the year after Cummings sold his second company for $95.5 million, he became a limited partner in Mosley Ventures.
Cummings isn’t the only investor Mosley helped get established in Atlanta. He is a venture partner with Zane Venture Fund and an adviser to Silicon Road Ventures.
Shila Nieves Burney, founder and managing partner of Zane, first found out about Mosley through a simple Google search in 2018: Who’s the best investor in Atlanta?
“So this guy, Sig Mosley, came up,” Nieves Burney said. She was working on her first investment deal and barely knew what venture capital was. But she knew she wanted to learn from the best. Mosley met with Nieves Burney for coffee, kindly turned down the deal she had pitched him, but said he was open to answering any questions she had.
“He should have never said that because anytime I had a question, I would ask him to meet me,” she said. But Mosley would always show up and over time became a mentor, and then a business partner.
When Nieves Burney was raising Zane’s first fund, Mosley had already paved the way for her. He gave her the name of someone to call and ask for an investment. When she did, the investor said, “You don’t have to pitch me anything. I’m in, Sig called me already. Just send me the wire information,” she recalled with tears in her voice.
“Sig has been in rooms talking about us, doing things for Zane that I’m not even aware of and probably won’t even see for a few years.”
Credit: Phil Skinner
Credit: Phil Skinner
Mosley’s reach has been so wide for founders and investors that there is even an annual honor named after him. The Siggie Awards celebrate outstanding early stage metro Atlanta investors. Instead of a statuette, winners receive a bobblehead of Mosley.
“Everyone just has such love for him, because he’s just done so much for the community, and I think he was really a pivotal part to driving our ecosystem,” said Allyson Eman, CEO of Venture Atlanta, one of the largest venture capital conferences in the country.
Mosley has also been on the board of the H.J. Russell Innovation Center for Entrepreneurs, the nonprofit focused on boosting Black entrepreneurship, since its inception. Jay Bailey, president and CEO of the center, called Mosley “omnipresent.”
“There have been so many encounters in so many different various spaces in Atlanta, before the Russell Center and beyond, where Sig is just in the midst,” Bailey said. “I don’t care if it’s a billion-dollar company, a billion-dollar idea or somebody that’s just got a few dollars in their pocket, Sig is really one of those individuals that’s going to show up.”
Only recently has Mosley decided to be “semiretired.” For him, it means he’s not making any new investments, not going to as many startup events and instead going on more vacations, but he is still highly involved in the startup scene.
Along with being part of Zane, Silicon Road Ventures and the Russell Center, he is entrepreneur-in-residence at three institutions, including Georgia Tech and Emory, is a member of Georgia State University’s cybersecurity advisory board and part of the Georgia Advanced Technology Development Fund at Georgia Tech.
That is his version of being “semiretired.”
Now, all these decades later, what keeps Mosley going is very simple.
“I enjoy working with the entrepreneurs I help. I enjoy getting companies built,” he said. “It’s something I enjoy doing.”
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